Luteic acid

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Luteic acid
Luteic acid Luteic acid.svg
Luteic acid
Names
Preferred IUPAC name
3,4,8,9,10-Pentahydroxy-6-oxo-6H-dibenzo[b,d]pyran-1-carboxylic acid
Other names
Luteolic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21)
    Key: FLZGFQFYDGHWLR-UHFFFAOYSA-N
  • InChI=1/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21)
    Key: FLZGFQFYDGHWLR-UHFFFAOYAI
  • C1=C2C(=C(C(=C1O)O)O)C3=C(C(=C(C=C3C(=O)O)O)O)OC2=O
Properties
C14H8O9
Molar mass 320.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid. [1] It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin. [2]

References

  1. ↑ Nierenstein, M.; Potter, J. (1945). "The distribution of myrobalanitannin". The Biochemical Journal. 39 (5): 390–392. doi:10.1042/bj0390390. PMC   1258254 . PMID   16747927.
  2. ↑ Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, INIST   19467830 (abstract)
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